


The Ideal Man

by DRHPaints



Category: American (US) Actor RPF, Bill Hader - Fandom, Bill Hader RPF, Saturday Night Live, Saturday Night Live RPF, US Comedians RPF
Genre: Backstage, Blow Jobs, Conan O’Brien - Freeform, Costume Kink, Costumes, Established Relationship, Explicit Language, Explicit Sexual Content, F/M, One Shot, Saturday Night Live References, Smut, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-09-22
Updated: 2020-09-22
Packaged: 2021-03-07 16:20:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,675
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26590525
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: When Gwendolyn brings Bill a late dinner before a taping of Saturday Night Live and stumbles upon him wearing the costume for his Conan O’Brien impression, Bill notices she gets incredibly excited.
Relationships: Bill Hader/Original Female Character(s)
Comments: 2
Kudos: 6





	The Ideal Man

**Author's Note:**

> If you’re a Bill and Conan fan and you haven’t seen the sketch referenced in this fic, do yourself a favor. Season 35 Ep. 12, Sigourney Weaver hosting, opening. Unfortunately I haven’t been able to find it on YouTube so I don’t have a link, but it is on Hulu (for the US at least) and let me tell you, ya boi screamed when he first saw the Glory that is the ConanBill.

Jogging down the hall, Gwendolyn placed a hand to the bottom of the bag of takeout, relieved to find it was still warm despite her lateness. Knocking on the dressing room door, a familiar, slightly nasal voice radiated through. “Come in.”

Out of breath, Gwendolyn twisted the knob, eyes closed as she burst in. “Sorry honey, they took forever with the beef...and..brocc...oli…” Voice trailing off, Gwendolyn took in Bill’s appearance and swallowed. Black suit. Blue button up. Red patterned tie. And to top it off, the iconic orange pompadour wig complete with ginger eyebrows.

“Oh it’s no problem, I’ve got time. Thanks, babe.” Bill took the bag from her hand, dipping down to give Gwendolyn a kiss on the cheek before he set the food in front of his mirror and rummaged inside.

“Are you…” Gwendolyn blinked. “Are you doing Conan tonight?”

“Oh.” Bill nodded, gesturing over himself. “Yeah.” Unearthing an egg roll, he bit in half, chewing and humming appreciatively.

Clearing her throat, Gwendolyn took a step toward him. “I...I didn’t realize you did a Conan impression…”

Shrugging, Bill finished the egg roll, wiping his fingers on a tissue so as not to mess up his costume. “Well, there’s not much to it, really. I found the hook pretty easily.”

Biting her lip, Gwendolyn folded her hands in front of herself. “Bill, I know you don’t like it when people ask you to do voices, but...could I hear it? Just a little? Maybe?”

“Sure.” Shrugging, Gwendolyn watched in amazement as Bill somehow managed to not only transform his voice, but even the muscles of his face, holding the lower tension around his mouth precisely in the way Conan did as he spoke in the late night host's reedy tone. “Alright everybody, now you know my next guest, he’s been in such movies as _Taxi Driver_ and _Heat_. Please welcome to the show, Robert DeNiro!” Bill even positioned his _hands_ like Conan, index finger gracing the corner of his lip.

With a coquettish giggle, Gwendolyn clapped her hands, jumping up and down excitedly. Bill looked at her curiously. They both enjoyed Conan, watching every episode of his show together, typically recording it because neither of them were home or awake when it aired. Sometimes they even used Bill’s Sundays off to watch three or four episodes at once, spending many an hour on the couch laughing at Conan’s antics. Through his time at Late Night, and now Conan’s brief run at The Tonight Show, he and Gwendolyn were loyal fans. Bill always assumed that, like himself, she liked Conan because he was _funny,_ but the look in her eye told a different story.

“Hey Gwen…” Narrowing his eyes, Bill blinked. “Do you have a little thing for Conan?” A wide smirk spread over Bill’s face.

Blush rising to her pale cheeks, Gwendolyn brought a hand to her face. “Little...might be a bit of an understatement…”

“What?” Giggling, Bill approached her, placing his large hands at her waist. “You never told me that.”

“I don’t know…” Peeking between her fingers, Gwendolyn saw Bill’s teasing grin. “I know he’s your friend and all. I didn’t think you’d like it if I told you I found him incredibly...sexy.”

“Oh really?” Corners of his mouth turning down in appraisal, Bill nodded as he drew her close. “I see how it is. Alright.” Slipping back into the Conan impression, he glanced at her with a raised eyebrow. “Nice to find out my girlfriend wants some ginger giant to bend her over his desk.”

Eyes widening, Gwendolyn’s hands slid up Bill’s chest. “I...I…” She swallowed. “I’m sorry, Bill. That’s…” Fingers tracing his sharp jaw, she stared into his cobalt eyes. “It’s extremely hot seeing you like this.”

Rolling his eyes, Bill shook his head, but Gwendolyn leaned in, warm body swiveling against him, her curvaceous lips brushing over the sensitive skin below his joined earlobe. “How...how much time do you have before the show?”

Peeking at the clock on the wall as he grabbed two handfuls of her ass, Bill pressed a kiss to Gwendolyn’s cheek. “A little over half an hour.”

Nodding, Gwendolyn dragged her teeth lightly over his neck, desperately wishing she could fist her fingers in the orange hair, but afraid to mess up the wig before Bill had to go on. “Let me suck you, Bill.” She breathed, hand trailing down the front of his body.

Dragging Gwendolyn close, Bill smiled mischievously, affecting the Conan voice once more. “Yeah, you want a big ginger cock in your throat, don’t you?”

Expecting her to laugh, when Gwendolyn’s breath hitched and she palmed him over the slacks, frantically capturing Bill’s mouth and walking him backward to the couch, he was a little taken aback but he certainly didn’t mind as he sat back and she straddled him. 

Tongues twirling, Bill inched his big hand up her creamy thigh, and dipping inside Gwendolyn’s panties he giggled against her lips when he discovered how wet she was. “Wow, you _really_ like Conan.”

Sitting back, Gwendolyn shook her head, eyes downcast. “I’m sorry, Bill…”

“Honey, it’s okay.” Bill smiled, patting her hip. “It’s not like I never find other women attractive, or anything.”

“That’s fair.” Gwendolyn peered into the distance, nodding, before she looked down into his dark blue eyes. “Don’t think I didn’t notice how you came home and mauled me after Blake Lively hosted last month.”

Shifting his eyes away guiltily, Bill shrugged. “Yeah, well…”

Chuckling, Gwendolyn claimed his light pink lips again, fingers undoing the zipper of his slacks before she shimmied down Bill’s body and knelt on the floor. Gwendolyn encouraged Bill to lift his hips and slid his pants down to his ankles along with his boxers, admiring the curve of his stiff erection laying before her. 

Encircling his cock with her fingers, Gwendolyn lowered herself and took the head into her mouth, sucking lightly as she pushed her tongue against his frenulum. Sinking down, Gwendolyn began jerking Bill’s shaft, hollowing her cheeks and using her other hand to caress and gently tug on his balls.

“Mmm...fuck Gwen, that’s good…” Gwendolyn would often visit him before tapings, and Bill was grateful that one of the ways she helped him with his anxiety was regularly fooling around in his dressing room. Fingers fisting in her crimson waves, Bill thrust into her warm throat, resting his head back and moaning.

“Fuck... _fuck, Gwen. Your mouth...fuck...don’t stop!”_ Bobbing rapidly, Gwendolyn paused, tapping Bill’s thigh. Hands releasing her, Bill whined as she rose. “Fuck, Gwen, _please…”_ Bill wriggled a little on the couch, squeezing her hand. 

“I’m sorry, Bill. And if you want me to finish you with my mouth I will. But…” Emerald eyes voracious, Gwendolyn stared at him, and when she spoke her voice was smoky, sultry. “I just want to fuck you so badly. _Please_ , Bill.”

“Yeah.” Nodding insistently, Bill gestured to her. “Climb on.”

Gwendolyn stood and hooked her thumbs under her panties, shoving them over her hips and kicking them away. Bunching her skirt about her waist, she tossed her legs over Bill, positioning herself over him and sheathing his thick cock inside of her in one fluid motion. “Oh Bill... _yes…_ ” Gwendolyn breathed. Immediately bouncing, her arms clung to Bill’s expansive shoulders as he twisted his heels into the floor, upper back braced on the couch as he clamped a hand to Gwendolyn’s hip, the other spinning over her clit as Bill pounded into her recklessly.

“ _Fuck, Bill! Yes! Fuck me! Just like that!”_ Slamming herself down, Gwendolyn fought to keep her eyes open, the combination of Bill’s handsome features sprinkled with the Conan hair, makeup, and the sharp suit deeply arousing. 

Bill’s blue eyes were stormy, elegant nose flared, pink lips curled into something resembling a snarl as he hammered his cock into Gwendolyn. “Yeah, you like that?” Growling, Bill rotated his hips as he rocketed forward, nailing her g-spot with every stroke and rattling high shrieks from Gwendolyn, forcing her to slap a hand over her own mouth. “You like the way I fuck you? Huh? _Huh?_ ”

Nodding enthusiastically, Gwendolyn screamed into her own palm as she leaned forward, arms pulling Bill near as she frantically ground her hips back and forth. Dragging her against himself, Bill and Gwendolyn humped wildly and as he sensed her fluttering around his cock, Bill hasted the fingers moving between her legs. 

Burying her face in his neck, Gwendolyn removed her hand, pulsing hard and fast in her final moments as tremors spread outward from her thighs and she cried out Bill’s name again and again into his flesh, body shuddering and eyes rolling.

Not far behind, Bill’s arms snuck around Gwendolyn as he shifted to the edge of the couch, hands locking over her shoulders to drive into her with abandon as he pushed his face to her collarbone. “ _Fuck, Gwen! I’m fucking cumming! Yes! Fuck!”_ Drawn out whimper growing in his throat, Bill’s hips lept irregularly and his hot cum drained inside of her. 

Afraid of staining his costume, Gwendolyn dismounted quickly, grabbing a couple of tissues from beside Bill’s mirror to clean herself before locating her panties and joining him on the couch. Zipping himself up, Bill saw it was almost showtime and stood to check himself in the mirror, glad neither the wig nor the eyebrows were knocked loose during their passion. 

After sharing a brief kiss, Gwendolyn gave Bill a hug, leaning back with a smile. “Have a good show, Bill.”

“Thanks, honey.” He grinned and she squeezed Bill’s arm. Bill took a couple of steps and started to open the door when Gwendolyn stopped him.

“Hey Bill?” She tilted her head.

“Hmm?” Bill glanced back over a broad shoulder.

“Do you think anyone would notice…” Raising her eyebrow, Gwendolyn chewed her lip. “If that wig went missing after you wrapped tonight?”

Rolling his eyes, Bill giggled, capturing Gwendolyn’s lips for one last kiss before he went out on stage.

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also take requests!


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